JPS6228763B2 - - Google Patents

Description

[Detailed description of the invention]

The present invention relates to a hair styling product. Hair styling products currently on the market include liquid hair liquids, hair tonics, paste pomades, solid sticks, and emulsified creams. Its components include a base component that has so-called hair-styling properties, a solvent, a fragrance, additives, and the like. Conventionally, various animal and vegetable oils and fats and mineral oils have been used as base components having hair styling properties, but in recent years, synthetic oils such as polyalkylene glycol compounds have been used. Among polyalkylene glycol compounds, polypropylene glycol and its derivatives are widely used. The physical properties required as a base material for hair styling products are that it has excellent hair styling ability, does not corrode celluloid and synthetic resins used as combs for glasses, and can be easily washed off when washing hair.
It is important that there is no irritation to the hair or scalp. However, among these physical properties, base materials with excellent hair styling properties have the disadvantage that they are difficult to remove when hair is washed, and base materials with good hair washing properties have poor hair styling properties, so a base material that satisfies all physical properties is desired. ing. Vegetable oils such as castor oil, camellia oil, and Japanese wax, and mineral oils such as liquid paraffin have good hair styling properties, but are difficult to wash off. Polyalkylene glycol base materials that have been used in recent years can be made by changing the degree of polymerization.
A base material having an arbitrary viscosity can be obtained, and by changing the type of alkylene oxide and the number of moles added, it is possible to obtain a desired base material from water-soluble to water-insoluble. However, no compound has been obtained that satisfies all of the properties of hair styling ability, celluloid erosion properties, and hair washing properties. The present inventors synthesized polyoxyalkylene glycols with different types and molar addition ratios of base alcohol and alkylene oxide,
As a result of intensive research, we have come up with the invention of a hair styling product base material that can simultaneously satisfy the above three properties. The hair styling product of the present invention has the formula RO(R′O) _a (C ₃ H ₆ O) _b H () (wherein R is a C ₁ to _{C 18} alkyl group, and R′O is butylene oxide or butylene oxide and propylene. A group randomly polymerized with oxide, a
and b are numbers from 1 to 124 and from 1 to 154, respectively, and are determined such that the weight ratio of butylene oxide and propylene oxide is 10:90 to 90:10 and the molecular weight is 500 to 10,000) It is characterized by containing one or more alkylene monoalkyl ethers. The polyoxyalkylene oxide monoalkyl ether shown in () above is methanol,
Butylene oxide is added to a C ₁ to C ₁₈ alcohol such as ethanol, butanol, octanol, lauryl alcohol, cetyl alcohol, 2-ethylhexanol, stearyl alcohol, isostearyl alcohol, etc., and then propylene oxide is added, or the above C ₁ ~ _C18
It is synthesized by randomly adding butylene oxide and propylene oxide to alcohol, and then adding propylene oxide. The weight ratio of butylene oxide and propylene oxide is 10:90 to 90:10, preferably 30:70 to
It is 70:30. When using propylene oxide alone or when the weight ratio of butylene oxide is less than 10%, the hair styling ability and celluloid erosion properties are inferior, and when using butylene oxide alone or when the weight ratio of butylene oxide is greater than 90%, the hair washing performance decreases. . Furthermore, a compound in which ethylene oxide is added after addition of alkylene oxide has too strong hydrophilicity, easily absorbs moisture, and has poor hair styling ability. The above-mentioned reaction between monohydric alcohol and alkylene oxide is carried out using an alkali catalyst such as potassium hydroxide or sodium hydroxide under normal pressure or increased pressure.
It may be carried out at 90 to 150°C under an inert gas atmosphere. The polyether () used in the present invention has a butylene oxide group in the chain and a propylene oxide group at the end, and the weight proportion of the butylene oxide group in the total alkylene oxide is 10 to 90%. There must be.
If this ratio is lower than 10%, hair styling properties and celluloid erosion properties will be poor, and if this ratio is higher than 90%, hair washing properties will be poor. Furthermore, in order to obtain satisfactory physical properties, the molecular weight of the polyether () must be between 500 and 10,000. When the molecular weight is less than 500, the viscosity is too low to be used as a hair styling product, and when the molecular weight is greater than 10,000, the viscosity is too high and it is unsuitable for use as a hair styling product. The polyoxyalkylene monoalkyl ether of the present invention can be used alone or as a mixture of two or more in the hair styling product base material. It may also be mixed with other types of hair styling material base materials. Other base materials to be mixed include a phosphoric acid ester of a compound of the above formula (), or a compound of the formula R[-O(R'O) _a -(C ₃ H ₆ O) _b H] _C (wherein R is C ₂ to C ₈ saturated hydrocarbon residue, R′O is butylene oxide or a group in which butylene oxide and propylene oxide are randomly polymerized, a and b are butylene oxide and propylene oxide in a weight ratio of 10:90 The molecular weight is ~90:10
A number determined to be 800 to 5000, c is 2 to
Examples include polyalkylene oxide polyols represented by (an integer of 8) or phosphoric acid esters of the above polyols. A high-quality hair styling product can be produced by blending water, ethanol, etc. with the hair styling product base material of the present invention. The hair styling product of the present invention satisfies all of hair styling properties, celluloid erosion properties, and hair washing properties when used. Hereinafter, representative examples of the present invention will be explained in more detail with reference to production examples and examples. Production Example 1 3 Put 148 g (2.0 mol) of n-butanol and 4.8 g of potassium hydroxide into a stainless steel autoclave, replace the gas phase with nitrogen gas, and then heat to 110°C. 1440g (20.0mol) of butylene oxide
Delivered under the conditions of 100-120℃, 6.5Kg/cm ² G or less,
In addition, 812 g (14.0 moles) of propylene oxide
After feeding under the same conditions, heat and stir for 2 hours under the same conditions. The reaction product was taken out, the catalyst was removed, and low-boiling substances were removed while blowing nitrogen under conditions of 90-100°C and 10 mmHg to obtain 2280 g of a pale yellow transparent viscous liquid. The hydroxyl value of the obtained compound is
It was 48.6 mgKOH/g. Production Examples 2 to 14 Polyoxyalkylene oxide monoalkyl ethers having the structure shown below were obtained by adding butylene oxide and propylene oxide to a base monohydric alcohol in the same manner as in Production Example 1 (Production Examples 2 to 10) ). In addition, these mixtures were manufactured using the following formulations (Manufacturing Examples 11 to 14).

[Table] Examples 1 to 14 Regarding the compounds and mixtures obtained in Production Examples 1 to 14 above, celluloid erosion properties, hygroscopicity, hair styling properties,
Hair washability was tested. The results are shown in Table 1. The evaluation method is as follows. (1) Celluloid erosivity Take 70 ml of a test solution containing the compound of the present invention: ethanol: water at a weight ratio of 15:50:35 into a 100 ml sample bottle, and add 20 mm x 50 mm x
After a 0.6 mm celluloid plate is immersed at 23±1°C for 96 hours, the change in weight of the celluloid plate is measured and the appearance is observed. In Table 1, the mark ○ indicates good appearance with almost no change, and the mark x indicates poor appearance (deformation). (2) Hygroscopicity Weigh accurately 7g of the compound of the present invention in a 100ml beaker, and place it in a desiccator containing a saturated ammonium sulfate solution (23±1°C, 80%RH) for 96 hours.The increase in weight is defined as the amount of moisture absorbed. (3) Hair styling property Compound of the present invention: Ethanol: Water weight ratio: 15:
A man's hair was treated with a 55:35 sample, dried with a hair dryer, and then conditioned at 23°C and 80% RH for 24 hours to observe changes. ○ mark in Table 1 indicates good hair styling properties.
An x mark indicates a defect. (4) Hair washability The sample tested for hair styling properties is immersed in a 5% aqueous solution of sodium salt of polyoxyethylene lauryl sulfate and stirred at 25°C for 5 minutes. Next, it was soaked in water and stirred at 25°C for 5 minutes, then washed with water three times and dried. This sample was immersed in ethanol for extraction and compared with an extract from untreated hair. 1st
In the table, ○ indicates good hair washability, ×
The mark indicates poor hair washability. Comparative Examples 1 to 4 The following compounds were manufactured by a method similar to the manufacturing method of the manufacturing example, and their performance was evaluated by the method described above. The results are shown in Table 1. 1.C ₄ H ₉ O (C ₃ H ₆ O) ₁₃₀ H 2.C ₄ H ₉ O (C ₄ H ₈ O) ₈₅ H 3.C ₁₂ H ₂₅ O (C ₄ H ₈ O) ₂₀ (C ₂ H ₄ O) ₁₀ H 4.C ₄ H ₈ O (C ₃ H ₆ O) ₁₀ (CH ₂ CH ₂ CH ₂ CH ₂ ) ₅ H

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Claims (1)

[Claims] 1 Formula RO(R'O)a(C ₃ H ₆ O) bH (wherein R is a C ₁ to _{C 18} alkyl group, R'O is butylene oxide or butylene oxide and propylene oxide) A group in which a is randomly polymerized, a
and b are numbers from 1 to 124 and from 1 to 154, respectively, and are determined so that the weight ratio of butylene oxide and propylene oxide is 10:90 to 90:10 and the molecular weight is 500 to 10,000). A hair styling product containing one or more oxyalkylene monoalkyl ethers.